(2S,8R,9S)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2'-yl)oxy)octan-1-ol | 1059187-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,8R,9S)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2'-yl)oxy)octan-1-ol
• CAS: 1059187-49-3
• 化学式: C₂₂H₄₆O₄Si
• 分子量: 402.69
• InChiKey: ILQNYDQURHIRON-NEAJECIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,8R,9S)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2'-yl)oxy)octan-1-ol 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到
  参考文献：
  名称：

  Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides

  摘要：

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.028
• 作为产物：
  描述：

  tert-butyl-[(2S,8R,9S)-1-[tert-butyl(dimethyl)silyl]oxy-8-methyl-9-(oxan-2-yloxy)decan-2-yl]oxy-dimethylsilane 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以70%的产率得到(2S,8R,9S)-2-((tert-butyldimethylsilyl)oxy)-8-methyl-9-((tetrahydropyran-2'-yl)oxy)octan-1-ol
  参考文献：
  名称：

  Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides

  摘要：

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.028